Volume 33, Issue 20
Preparative Organic Chemistry
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ChemInform Abstract: Dramatic Influence on the Olefinic Geometry in the Nickel(0)-Catalyzed Coupling Reaction of 1,3-Dienes and Aldehydes Using N-Heterocyclic Carbene as a Ligand.

Yoshihiro Sato

Yoshihiro Sato

Grad. Sch. Pharm. Sci., Hokkaido Univ., Sapporo 060, Japan

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Rieko Sawaki

Rieko Sawaki

Grad. Sch. Pharm. Sci., Hokkaido Univ., Sapporo 060, Japan

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Miwako Mori

Miwako Mori

Grad. Sch. Pharm. Sci., Hokkaido Univ., Sapporo 060, Japan

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First published: 21 May 2010

Abstract

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ChemInform Abstract

Coupling of diene (I) with aromatic aldehydes and silane (III) in the presence of an in situ generated catalytic Ni(0)—heterocyclic carbene complex proceeds with absolute (Z)-stereoselectivity. Since the analogous reaction in the presence of a catalytic Ni(0)—phosphine complex furnishes the coupling products with (E)-selectivity (presented previously), a different reaction mechanism must be proposed.

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